Chicago Recommendations

Chicago is known as the windy city, not because of its wind, but because of its terrible politics. That said, if you visit between late September to April, bring winter wear.

Also, some of my information may be out of date. I lived in Chicago for the summer of 2014, and went back for a week in 2015 and 2017. I would love to make plans to come back.

Where to Stay

• If you’re looking for a cultural area to stay in, Little Village is known for Chicano culture and was highlighted in a talk Morgan and I went to at her sociology conference
• I’ve stayed in Lincoln Park, Lakeview, and Skokie
  • Lincoln Park is a rich area, so if you’re willing to pay more for a nice lake view, that’s a great area
  • Lake View is the neighborhood from the TV show “Family Matters” with Urkle. It’s next to Wriglyville, so if you’re looking to stay next to the ballpark and a bunch of nightlife and bars, that’s where it’s at
  • Skokie - Unless you are going to Evanston where Northwest is, or have any business being in the suburbs, there isn’t much to do
• Other notable areas
  • Logan Square - if you’re looking for a multicultural neighborhood full of community, nightlife, food and drinks, this is the place to be.
  • Boystown / Northalsted - a great LGBTQ+ community much like the Castro. During pride month, there’s a lot of celebrations

    one of the most country’s inclusive LGBTQ+ communities and the oldest officially recognized gay neighborhood in the United States. It’s known for its welcoming vibe, nonstop nightlife, LGBTQ-owned businesses, and excellent dining options. It’s also the center of some of Chicago’s most popular events and festivals.

• Avoid: South Side, unless you’re going with someone who lives there

Exploring

Chicago is super walking and transit friendly. Since the city sold their parking meters to a bank, it’s super expensive to park around the loop (i.e. the downtown and Millennium Park). I recommend CTA’s L Train to get most anywhere you need to go and walk from there. If you stay in any of the above, there’s a huge chance the L will run near it.

Cultural and Seasonal

I already mentioned Pride month. During the summer, you’ll find block parties as well.

Music is huge in Chicago, whether that’s music festivals like Lolapallooza, Riot Fest, Pitchfork, or checking out the House of Blues, and far too many music venues to list.

There are so many cultural enclaves when you explore Chicago.

• Chinatown - I’d be remiss if I didn’t mention it. It’s certainly not bay area big, but it’s notably big for the mid-west. Again, that’s not saying much as I thought this should have been bigger. I’ve had dim sum here as well as a haircut, and they were pretty comparable to the Manhattan Chinatown. But not Flushing. That’s a whole lot bigger.
• Greek - I accidentally stumbled into the greek festival, and they’ve got their own community. Also, My Big Fat Greek Wedding takes place in Chicago.
• Polish - I was surprised how prominent polish people were in Chicago. I had my first Pierogis here. I think I went to Polombia, which combines Polish and Colombian food.
• Ukrainian Village - I didn’t know this existed before. I’ve been meaning to check it out
• Little Village - I mentioned it in the places to stay. “La Villita” is also worth exploring for the art, food, and nightlife.

If you’re a comedy fan, there are great live shows from Second City. There are many prominent names who’s come out of here, including Stephen Colbert, Steve Carell, Tina Fey, and Amy Poehler.

If you want theater, they have their broadway and off-broadway shows as well.

Year Round Places to See

• Navy Pier - Like Santa Monica Pier, and less dingy than Coney Island
• Field Museum - I loved this museum. Sectioned off into many exhibits. Worth it.
• Art Institute of Chicago - I’ve heard a lot of good things from others about this, but haven’t been myself
• Logan Square
• Millennium Park and the Bean - during the summer, I recall they have movie in the park. Of course, you can get up close to the bean
• The Waterfront - If you love running, this is probably the best place to run. It runs adjacent to Lake Michigan, and is quite a site to view all of Chicago’s skyscrapers

Foodies Beware

Chicago is a food hub for some serious high-end restaurants, as well as some great local staples. Since you have to reserve far in advance for some of these, I’ll leave the high end ones at the front.

• Alinea - Chef Grant Achatz’s innovation to modernist cuisine has been universally praised. It’s a restaurant where the kitchen is far bigger than the dining area, and they have limited seats per night.
  • As an aside, they also have off-shoots, like cocktail bars called the Aviary and The Office. I’ve heard great things about this
• Girl and the Goat - Chef Stephanie Izard’s restaurant known for its roasted pig’s face. If you’re seeking a restaurant known for cooking with the whole animal, it’s this place.
• Honestly, I can’t list them all, so here’s a primer list.

For more common day food, Chicago has a lot to offer.

If you’re looking for that Chicago deep dish, the easiest place to find it is in a chain of restaurants called Lou Malnati’s. Order ahead, as it may take up to 30 minutes for them to bake it. There’s of course a ton of other options. I know on my list to check out is Burt’s Place where they serve it to you in the pan.

The other prominent Chicago-esque food is the Chicago Dog. I personally don’t care for it as much as others do, but if you like this pickle hot dog contraption, check out Fastso’s Last Stand. Also, other places.

Resources

• Wikivoyage - Chicago - I think WikiVoyage has some great breakdowns of major metro hubs. Chicago is very diverse, and you should get to know its different neighborhoods before going. Setup a short itinerary as it can be a lot to take in.